How to Make a Career Transition Without Sacrificing Your Past Experiences

Let’s face it — you want to switch career paths.

Yet you’ve already put in thousands of sweat-inducing hours of work to improve your craft.

Others may see you as an expert, but beneath the accomplishments, you’re secretly feeling more and more dissatisfied with the nature of your work.

There’s a lingering dream of answering a creative calling. You want a new professional challenge. You want to do work that’s aligned with your strengths.

What do you do?

How do you make the transition to a brighter, more fulfilling career path without giving up your hard-earned experience over the years?

Fortunately, there’s a simple solution. It’s also what I did during my own career transition from marketer to product manager.

Here it is:

Talk to high-performers in your desired field who have made a similar transition. Get their feedback on your positioning and experience map.

Not too complicated right?

Let’s dive right into looking at how each part of this solution works in practice.

Step #1: Create a straw man version of your positioning & experience map

Based on what you already know about this target role, identify the characteristics you think the hiring managers are looking for in high-performing candidates.

Are they looking for a deeply analytical skillset? Are they looking for someone scrappy, who can find ways to get things done through low-cost, non-obvious means?

Step into the hiring managers’ shoes for a moment, and imagine what they would care about seeing in a new hire. Use those empathy muscles!

Brainstorm for a few minutes. We’ll use this list to shape your positioning and experience map.

Narrow down your list to just the characteristics that match your strengths. These are the strengths you want to highlight in stories you tell during interviews, coffee chats, and even on your job search documents.

Now take another cut of just the characteristics where you feel the weakest. These are likely the gaps you have that would benefit from gaining fresh experience.

Step #2: Reach out to high-performers in your target field

Leverage your existing network at first — friends, friends of friends, colleagues, classmates, the barista from your favorite cafe…. (half-kidding)

What if you don’t know anyone in your target field?

Find people on LinkedIn doing your dream job and cold email them to set up a short coffee chat. Personalize your message.

Here are a few tactical tips:

• Send emails, not InMails, because the former typically get higher response rates.
• Make a list of the target roles you’re excited about. Email at least 30-40 people working in these target roles. For every 10 people, expect 2 to get back to you (20% response rate).
• Be patient. When you just start out, you might hear crickets. Don’t give up. Keep improving your process.

Once you’re sharing a cappuccino together, don’t be shy about showing your enthusiasm. One of the most flattering things is hearing and seeing genuine curiosity in what one does.

Don’t be afraid to share your own unique stories and experiences — they have something to learn from you as well.

At the end of each conversation, ask your new acquaintance for recommendations of other talented people they know in the field to speak with. Reach out to them.

Step #3: Get feedback on your positioning and experience maps

High-performers in their field can give you valuable insight into whether or not your positioning and experiences are going to meet the hiring bar and set you up for success in the job.

Follow-up after your initial coffee chat, asking if you can share with them 2-3 of the stories you plan to share during your interviews. What would they tweak or improve about your stories given what they know about the role and you?

Send them your thoughts on what you think are the most valuable experiences that hiring managers look for and what you think are your gaps. Do they think you’re right, or is there something they would correct about your assumptions?

There’s a lot of unknowns at play when you’re transitioning to a new role, so it’s super valuable to get the input of a high-performer who can illuminate the path forward for you.